Fatty acid amide derivatives



P 2,932,666 Ice Patented Apr. 12, 1960 i The free base may be preparedby reacting dl-trans-Z- amino-cyclohexan-l-ol withN-methyl-N-chloro-acetyl- 2,932,666 omega-phenyl-tert.butylamine, at amolar ratio of approx- I imately 1:2. The solvent medium may be butanoland the FATTY ACID AMIDE DERIVATIVES 5 reaction is carried out in thepresence of an acid-binding Meier E. Freed, Philadelphia, Pa., assignorto American agent such as alkali-metal carbonate or bicarbonate. The

Home Products Corporation, New York, N.Y., a correaction proceeds atreflux temperature. poration of Delaware The following exampleillustrates the procedure in N0 Drawing. Application August 7, 1958greater detail Serial Na 753,653 7.5 grams (0.05 mole) ofdl-trans-2-auuno-cyclohexan- 1-ol hydrochloride was dissolved in 250 cc.n-butanol. 30 2 Claims. (Cl. 260--559) grams sodium carbonate was addedand suspended by stirring. 24 grams (0.1 mole)N-methyl-N-chloroacetylomega-phenyl-t-butyl amine was added and themixture This invention relates to fatty acid amide derivatives refluxed18 hours. After cooling the reaction mixture and more particularly to adi-fatty acid amide and salts was filtered, the filtrate treated withdry hydrogen chloride thereof. and refiltered. The filtrate wasconcentrated to syrup un- Poly-fatty acid amides are known to the art,as evider vacuum and crystallized from ether-hexane mixture.

denced by various patents. These amides are stated to Product wasfiltered olf, Washed with acetone and dried. be useful in the textileindustry as softeners or dispersing 20 Yield: 9.5 grams, M. PL: 126 C.Free base (from hexagents probably because the compounds containlongane) M. Pt. 108-1085 C.

chain aliphatic radicals and therefore impart to these Analysis-Fm. 74.0C; 9.01 H; 8.06 N. Cale. 73.75

amides interface modifying action. In these disclosures C; 9.06 H; 8.05N.

no mention is made, nor has it ever been ascertained, that Theacid-addition salts of the base may be prepared in these compoundspossess pharmacological activity. any known manner, either by reactingthe free base with Later discoveries have shown that some classes ofdithe desired acid in a suitable solvent, or by a metathetic fatty acidamides do demonstrate therapeutic activity. reaction utilizing a salt ofthe base with a salt of the de- Thus, Martin et al.., in Patent No.2,411,662, disclose the sired acid in a solvent medium. Any acid,organic or inpreparation of a large number of amides all stated to haveorganic, may be used which forms a salt that is non-toxic an analepticaction. On the other hand, a patent has at the dosage level deemeddesirable. Thus, such acids as recently been issued to Seifter et 211.,2,780,646, discloshydrochloric, sulfuric, phosphoric, acetic, tartaric,citric,

ing a group of di-fatty acid amides having potent local etc., makeuseful salts.

anesthetic action. This application is a continuation-in-part ofapplica- It is pointed out in the aforesaid Seifter et al. patent, tionSerial No. 696,621 filed November 15, 1957, now and it has beencorroborated, that there is little predicabandoned.

tion with respect to the pharmacological activity noted. I claim:

Thus, as this patent points out, an amide having an alco- 1. A compoundof the group consisting of a di-fatty holic radical of 2 to 4 carbonsshows efiective anesthetic acid amide and the nou-toxic,pharmacologically acceptaction but a substantially similar amide havinga hexable, acid addition salts thereof, said amide having the anolradical does not have this utility. formula The present invention dealswith the discovery of a CH cyclohexanol di-fatty acid amide showingpotent local H C0 a anesthetic action. The compound,dl-trans-2-N,N-di[N- CHPOH, C methyl-N-(omega-phenyl-tert.butyl)-acetamido]amino- H Hl)aCH:- cyclohexan-l-ol, having the formulaCH CHPCH! 8 H (EH10 ON\ G(CHa)r-CH: QCIFN 2. As a new compound,2-N,N-di-[N-methyl-N- GHz-C (omega phenyl tertbutyl) acetamido]cyclohexan CHiCON 1 H o amine.

O(CHa):OH1

References Cited in the file of this patent and acid-addition saltsthereof have been found to possess 1 strong local anesthetic action andthus is deemed to have UNITE? STATES PATENTS utility as a specialanesthetic in either veterinary or human 2,411,662 M rtin et al- Nov.26, 1946 medicine. 2,780,646 Seifter et al. Feb. 5, 1957 UNITED STATESPATEN T OFFICE Certificate of Correction Patent N 0. 2,932,666 April 12,1960 Meier E. Freed It is hereby certified that error appears in theprinted specification of the above numbered patent requiring correctionand that the said Letters Patent should read as corrected below.

Column 1, lines 46 to 53, and column 2, lines 4-1 to 48, claim 1, thefirst two-thirds of the graphic formula, each occurrence, should appearas shown below instead of as in the patent:

/OHa OH CH maroon 5* (CHa)r Hie CH-N on ofi 2 1 omcoN owner same column2, line 39, claim 1, for acid addition read -aoid-addition.

[SEAL] Attest: KARL H. AXLINE, ROBERT C. WATSON, Atteszfz'ng Oficer.Gammz'ssz'onar of Patents.

1. A COMPOUND OF THE GROUP CONSISTING OF A DI-FATTY ACID AMIDE AND THENON-TOXIC, PHARMACOLOGICALLY ACCEPTABLE, ACID ADDITION SALTS THEREOF,SAID AMIDE HAVING THE FORMULA